


Five Times Dean Was Left Hanging And One Time He Wasn't

by LadyDrace



Category: Supernatural
Genre: Awkward Sexual Situations, First Time, Humor, M/M, Oral Sex
Language: English
Status: Completed
Published: 2012-09-06
Updated: 2012-09-06
Packaged: 2017-11-13 17:01:01
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 2,322
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/505738
Author URL: https://archiveofourown.org/users/LadyDrace/pseuds/LadyDrace
Summary: <blockquote class="userstuff">
              <p>It would seem the universe is on a mission to give Dean Winchester blue balls.</p>
            </blockquote>





	Five Times Dean Was Left Hanging And One Time He Wasn't

**Author's Note:**

> Beta: Mithrel looked it over for me. Thanks!

#1:

The first time Dean and Castiel had sex, Dean had been prepared for things to go a little bumpy. No matter how much Castiel assured Dean that he was perfectly aware of what happened during intercourse, Dean knew all too well that there was a major difference between knowing and doing. First times were always a little tricky.

Bolstered by this knowledge, Dean wasn't exactly shocked when things came to a really abrupt end before they'd hardly begun. After all, Castiel might be the 1000-year old virgin, but he had about as much understanding of - and therefore about the same level of control over - his human body as a 13-year old. So while he _was_ mildly disappointed when Castiel came all over him with a strangled sob after barely a minute of attention from Dean's hand, he would have been fine with just a little reciprocation. What he was very much _not_ fine with was how Castiel froze and blushed wildly, only sparing a panicked glance for Dean before disappearing into thin air, leaving Dean to take care of business on his own.

To make matters worse, he'd been so annoyed he'd refused to actually bring himself off and as a result of this he'd been cranky and wound up for hours, snapping at Sam and generally being a dick. Then of course hunting had gone absolutely bonkers, and weeks went by before they even got a chance to talk about it, much less try and patch things up.  
 

 

#2:

When they finally managed to find time and privacy for a second attempt, Dean decided to skip the talking and just pulled Castiel into the shower with him. This would normally have been an excellent idea, but of course, this _would_ be the one time where logistics were completely against Dean. In a series of freak events, they somehow managed to dislodge the little corner shelf that held soap and shampoo, one of the bottles splitting open as it hit the floor of the shower stall. Even Castiel's angelic skills never prepared him for exactly how slippery half a bottle of body wash could be. So consequently Dean slipped, and pulled the somewhat sex-addled angel down with him.

Afterwards, while he was holding an icepack to his head, he consoled himself with the fact that at least this time Castiel was left unsatisfied as well. It certainly did a lot more for his mood than Castiel's constant apologizing, which went on for quite some time.  
 

 

#3:

At last things were going according to plan. Dean was happily occupied blowing Castiel, and apparently sometime in between their first awkward sex-capades, Castiel had found a little self control, because he was managing to hold off his climax, even though Dean was using some of his best tricks. It was a close thing though, and Castiel was gasping and groaning continuously through the whole thing. It was doing wonders for Dean's ego and it was pretty much perfect how Castiel would pull Dean's hair just a little painfully when he tongued exactly the right spot under the head of his cock.

“Dean... I'm- _oh_!” Castiel panted and Dean bobbed his head a little faster. He was so keyed up from his pent up frustration and all those wonderful little noises Castiel was making that he would probably come all over himself with the smallest touch. But he was determined to get Castiel off first. It was a matter of personal pride. Castiel started shaking and was almost hyperventilating when he neared his breaking point.

“Dean! Oh, oh, _oh_! I... I'm...” Castiel was getting louder and Dean was starting to feel lightheaded with how good it felt, knowing he was the one making Castiel fall apart.

“Dean, Dean, Dean, DEAN!”

“... _Dean?_ ”

That _wasn't_ Castiel, Dean registered vaguely, before there was a careful knock on the door. Dean pulled off Castiel's cock with a wet slurp, intending to tell Sam to fuck off, but then everything happened at once. There was a hot spurt right across his cheek just as Castiel practically yelled: “ _I'm coming!_ ”

There was a very pregnant silence for about five seconds and then Sam's shaky voice drifted through the door. “I'm going to assume that _didn't_ mean someone coming to get the door... and... I'm gonna go scrub my brain now.”

When Castiel was finally done twitching through his climax and raised his head, he was met by the sight of Dean's face painted liberally with stringy, white streaks, a baffled expression settling there. The combination of come dripping into his eye and the sound of his little brother's horrified voice was enough to kill Dean's libido for the time being, and despite Castiel's earnest, but clumsy attempts he was simply unable to get back in the mood.  
 

 

#4:

While the fourth incident in the frankly disturbing pattern of Dean getting cockblocked _was_ wildly aggravating, it was merely a downside to their profession, with no guilt easily placed on anyone but the demons who chose to descend on them, just as Dean managed to get Castiel vertical again. The good news was that this time they were at least partly dressed, so Sam didn't have to go bleach his eyeballs after he kicked down the door to come help kill the creeps. That didn't stop him bitching, though, and it was only Castiel's warning grip on his arm that stopped Dean from saying something truly unkind to his brother about where he could stuff his complaints about Dean's sex life.  
 

 

#5:

By the fifth time, Dean was just about to give up on the entire idea and simply accept that the only action he would ever get would be from his own hand. It would seem the universe itself was out to ensure Dean's demise from a severe case of blue-balls. Had there been anyone to blame, Dean would surely have committed murder when he was once again cut off mere moments from his much needed release.

It was _really_ good. He and Castiel hadn't even made it to the bed, Dean's desperation not really allowing for anything more fancy than frantic rutting up against the nearest wall. Luckily, Castiel had been totally fine with that plan, and happily provided both delicious friction from his hand firmly down Dean's jeans, and the added bonus of heated moaning right into Dean's ear. He was _so_ close. Everything was hot and perfect, the rain and thunder outside completely inconsequential. At least until lightning struck. Years later Dean would laugh at the obvious irony of the situation, but at the time he was really expecting a whole different kind of lightning strike, and was not at all pleased when the sparks flying from every appliance in the room _wasn't_ in fact an orgasm-induced hallucination. He could probably have ignored the electric surge and the following darkness. What he could _not_ ignore was the frigid shower he was suddenly surprised with when the sprinkler system apparently went haywire, and doused the room in water so cold it felt like little razor blades where it hit his skin.

There was no end to his rage when he realized that Sam's room had _not_ been flooded, and that they would have to share for the night, thus killing every last hope he had of finishing anything. The only positive thing about that entire abysmal night was the fact that the drinks machine had also been zapped and was spitting out cans of beer in a steady flow. Dean scooped them up and brought them to the Impala where he proceeded to get drunk and wallow in his frustrated misery.  
 

 

#5-4-3-2-1-0

For a couple of days after that, Dean determinedly kept himself from trying to get Castiel alone again. He spent a little quality time with Busty Asian Beauties, so he at least wouldn't have a freakin' aneurism from pent up sexual frustration. But he was still so dismayed about the whole thing that he couldn't even bring himself to try anything when Sam was suddenly gone for an entire night, and Castiel was sitting next to him on the couch, watching Dr. Sexy with him. It was actually comfortable in a domestic kind of way, just sitting there together, elbows brushing every time Dean lifted his beer to his lips. Castiel even seemed to be trying to understand the action on the screen, but from the way he was squinting and tilting his head, Dean assumed he wasn't having much luck.

Evidently Castiel gave up on it eventually, because suddenly he slid off the couch and onto his knees in front of Dean, pulling off the trench coat he had stubbornly kept on all night. Dean felt his jaw drop open as Castiel let his hands glide from Dean's knee to his waist, not hesitating before thumbing open his jeans, and pulling Dean a little closer by his hips. He slouched back into the couch and hurriedly put aside his beer when Castiel bent down and simply nuzzled Dean's rapidly hardening cock through his boxers.

There was something dizzyingly unreal about seeing Castiel, _Angel of the Lord_ on his knees in front of him, but damn if it wasn't hot enough to melt his brain, even though nothing had really happened yet. All right, that wasn't strictly true, because from the sensations shooting through Dean's groin, he would argue that something was _definitely_ happening.

Castiel spent some time basically just rubbing his face all over Dean's crotch, and while it occasionally looked a little ridiculous, there was no denying that it felt damn good. So good in fact that Dean heard himself panting harshly by the time Castiel's long fingers finally curled around the waistband of Dean's boxers, and pulled them off his straining cock. Then there was a vaguely awkward moment where Castiel just looked at it, and Dean squirmed a little under the intense gaze. But in short order, Castiel grasped the length firmly, and boldly licked a broad, wet stripe across the head with the flat of his tongue.

Dean groaned and let his eyes slip closed. There was _no way_ he could watch that without cutting things _very_ short. Although, the past occurrences did give that option some merit. But this was _Castiel_ doing completely filthy things to Dean, and he really wanted it to last as long as possible, even at the risk of not getting off yet again.

Luckily, Castiel didn't seem to be in any sort of hurry either, and leisurely licked his way around every inch of Dean's aching flesh. It was sweet torture, and Dean couldn't help the way his hips jerked slightly whenever Castiel found some really good spots. Castiel seemed encouraged by it, and made little happy huffing noises through his nose, while holding Dean steady with a hand on his hip. Groaning in surrender, Dean just let Castiel do whatever the hell he wanted. There was no real technique applied, just honest curiosity and enthusiasm, and coming from Castiel it meant so much more to Dean than any other inexperienced partner he could ever remember being with.

He clutched at the couch cushions when Castiel suddenly swallowed him down, almost to the root. He didn't gag, even though Dean could feel the head of his cock bump firmly against the back of Castiel's mouth. One hearty swallow, and then the last inch was sucked into the furnace heat of Castiel's mouth as well. Dean groaned and tried desperately not to buck his hips, but Castiel swallowed again and pulled Dean closer by the hips. And as much as he wanted to be, Dean was just not gentlemanly enough to refuse such a blatant invitation. He pulled out a little bit and cautiously slid back in. Castiel swallowed happily around him, and then Dean lost it a little.

He took hold of Castiel's hair, threading his fingers through the messy locks, and started thrusting carefully, choking on his every breath, because that right there was just too damn good. Dean tried making a mental note of asking Castiel where he'd picked up that particular trick at a later date, but Dean's mind was mostly melted at this point, so there was no knowing if he'd remember it at all. Castiel kept encouraging him with eager bobs of his head, and hands pulling at his hips, so Dean let himself fuck Castiel's face freely. Then he made the mistake of looking down.

Castiel was blushing, the pink flush of arousal spreading down his neck, disappearing under his collar. His tie was even more messy than normal, and the top button of his shirt had come undone, showing off just a hint of tantalizing collarbone now and then as he moved. And even though he was clearly very much into what he was doing, his eyes were wide open, and firmly fixed on Dean.

That was it. Game over. Dean choked out a garbled sound that may have been Castiel's name, before letting his head fall back and finally - _finally -_ coming his brains out. Castiel hummed happily around the jerking length, and swallowed every last drop, making Dean shudder at the movements of his throat.

He let go of Dean's cock with a final lick to the tip, and Dean let out a loud breath before realizing he was still clutching Castiel's hair, and slowly disentangled his fingers. Castiel sat back on his knees, just watching as Dean got himself together again. A few breaths later Dean's brain started working again, and he yanked Castiel up onto the couch, and kissed the taste of himself right out of Castiel's mouth.

“I trust,” Castiel murmured between kisses, “that was... satisfactory?”

Dean couldn't help but laugh. “Jesus, Cas... if you really have to ask, I think we have a lot of work ahead of us.”

“I'm looking forward to it,” Castiel said seriously, and Dean decided that so was he.

End.


End file.
